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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
2 bedrooms, 3 beds, 1 private bathroom
27 Aug – 1 Sept
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4.82 out of 5 average rating, 199 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Aug
4.93 out of 5 average rating, 389 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
20–25 Aug
New place to stay
Guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 92 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Featured hotel
Room in Key Largo
Waterfront suite 9
1 bathroom
23–28 Aug
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
19–24 Aug
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 5 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds, 2.5 bathrooms
22–29 Aug
4.98 out of 5 average rating, 90 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
19–26 Aug
New place to stay
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 275 reviews
Top guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
9–14 Oct
5.0 out of 5 average rating, 91 reviews
Top guest favourite
Guest suite in Tavernier
Key Largo! Tavernier! Welcome to Paradise!
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 349 reviews
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 96 reviews
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
3 queen beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Key Largo
Your Keys Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.9 out of 5 average rating, 461 reviews
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed, 1 bathroom
17–22 Aug
Featured hotel
Room in Key Largo
Dolphin suite
2 double beds, 1 bathroom
17–22 Aug